The Contribution of cocoa additive to cigarette smoking addiction

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Page 142 of 207 RIVM report 650270002 Phenylethylamine 3.8 Phenylethylamine GENERAL IUPAC systematic name: phenethylamine (1) Synonyms: benzenethanamine-; beta-(aminoethyl)benzene (1) Molecular formula: C8H11N (1) Molecular structure NH 2 Molecular weight: 121.18 g/mol (1) Alifatic: yes, ethyl group (1) Aromatic: yes, phenyl group (1) N containing: yes, amine group (1) Halogen containing: no CAS registry no.: 64-04-0 (1) Storage: R/S classification: R 22-34 and S (01/02)-26-28-36/37/39-45 (2) dangercode (transport): 80 (2) Properties: melting point: -60ºC (2) boiling point: 197 – 200 ºC (1), 198ºC (2) density: 0.958 g/ml (2) refractive index: 1.529 º at 25 ºC (3) solubility: 4.3 g/l water, soluble in ethanol, ether, tetrachloromethane (2) substance description: color: colourless to light yellow (2) liquid/gas/powder: liquid (2) odor/taste: amine-like odour, smell of fish (2) volatility: slightly volatile (2) pKa: 9.84 (3) PA: 936.2 kJ/mol (4) flammability: FP = 90 ºC (1) and another source states 80ºC (2) FL Limits = no data available IT = 425 ºC (2) decomposition temperature: stability: unstable on exposure to air (2) vapour pressure/ vapour tension (20 °C): 0.298 mmHg (40 Pa) at 25 ºC (4) vapour pressure (50 °C): 500 Pa (2) relative density: 0.96 (2) octanol water partition coefficient, log P, log KOW: log P is 1.41 (1) conversion factor: not relevant Critical assessment Phenylethylamine is an endogenous amine related structurally and pharmocologically to amphetamine (5). The aliphatic bound amine group is chemically the dominant

RIVM report 650270002 Page 143 of 207 Phenylethylamine feature, immediately followed by the presence of the phenyl ring. The amine group supplies the compound with its base character, enabling it to react with acids: adduct formation with hydrochloride results in the well-known salt. At the other hand the benzene ring provides the aromatic feature to the compound. Conclusion Being an endogenous amine, phenylethylamine has an aliphatic base character while at the same time the structure contains an aromatic part. It readily forms a salt with an acid. FUNCTION IN TOBACCO No data available. AMOUNT IN TOBACCO PRODUCTS Phenylethylamine was found in several parts of Nicotiana tabacum cv Xanthi n.c. plant. Depending on the development and the part of the plant it varies between 58 – 400 nmol/ g fresh weight (7.0 – 48.5 µg/g fresh weight) (6). Assuming the dry weight of tobacco is 10 % of the fresh weight and phenylethylamine is not degraded during fermentation process, than we conclude that the estimated phenylethylamine amount in dried tobacco plant is between 70 - 485 µg/g dry weight. Assuming 1 g tobacco is used in cigarette, then the phenylethylamine level in one is cigarette is estimated to be between 70 µg and 485 µg. Phenylethylamine is also added to tobacco as a component of cocoa, which is used as a flavouring agent. A typical casing concentration of cocoa for cigarette tobacco is 1% (7). In cocoa phenylethylamine ranged from 0.22 µg/g to 22.0 µg/g (8). Assuming one cigarette weights approximately 1 g, the maximum phenylethylamine amount from cocoa in one cigarette is estimated to be 220 ng. The maximum natural phenylethylamine amount in cigarettes from tobacco plant is about 2200 times higher compared with the maximum phenylethylamine amount from added cocoa. AMOUNT IN SMOKE main stream No data available. side stream No data available. SOURCE Phenylethylamine is an natural tobacco component (6) and is also added to tobacco as a component of cocoa powder, which is used as flavouring agent (7). ENVIRONMENTAL LEVELS AND HUMAN EXPOSURE The mean phenylethylamine concentration which was determined in some English cheese ranged from 6.1 – 11.3 mg/kg (8). Phenylethylamine was also found in sauerkraut (2 mg/kg), Dutch cheese (9 mg/kg) and fermented sausage (14 mg/kg) (9). COMBUSTION PRODUCTS No data available.

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serotonin

caffeine

histamine

phenylethylamine

tryptophan

anandamide

tryptamine

tyramine

theobromine

rivm

contribution

cocoa

additive

addiction

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